“I Think I’ll Just Stay Here and Drink”

1980

Merle Haggard was an outlaw before there was a movement, and not just because he did time: He was a sensitive, thoughtful singer-songwriter with a romantic, chip-on-his-shoulder masculinity and rock ‘n’ roll swagger, and he released a tribute to Bob Wills years before Waylon declared the Western musician “still the king.” By 1980, outlaw country was past its commercial peak, but Merle just carried on as he always had with “I Think I’ll Just Stay Here and Drink,” a barnburner that nails the hard-swinging, improvisational approach of his live shows.

Here, Haggard is at a bar, stewing over a woman who doesn’t care what he thinks but, he says, couldn’t change his mind even if she did. That premise, though, is really just an excuse to let the band go. Fully three minutes of this rowdy four-and-a-half minute track, an eternity for country radio, is stuffed with solo after thrilling solo—electric guitar, piano, more guitar, saxophone, still more guitar. When they couldn’t land on a shorter edit he liked, Merle said, essentially, screw it, just press it and let the DJs deal with it. It went to Number One. –David Cantwell

“Guitar Town”

1986

The debut album by Steve Earle was a long time coming. More than a decade before its release in 1986, the Virginia-born songwriter ran away from home and began searching for his hero, Townes Van Zandt. Once he got to Nashville, not only did the young prodigy work with Townes but he also ended up recording with Guy Clark, writing songs for Carl Perkins, and appearing among his heroes in the definitive country documentary Heartworn Highways. So, when Earle finally got the spotlight and his own record label, how did the young country lifer introduce himself? “Hey pretty baby, are you ready for me?/It’s your good rockin’ daddy down from Tennessee.”

As far as origin stories go, the title track to Guitar Town is humble but prescient. More interested in the gritty Americana-influenced rock that Bruce Springsteen had been honing throughout the decade, Earle quickly steered clear of the pearly sheen and dead-eyed twang of so much ’80s country music. While Guitar Town still bears that pristine ’80s sound, you can hear Earle trying to shed it off in those constant grunts and “ha’s!” between his words, like he’s still working this all out. He’d get darker and more political with time; for now, he just wanted to rock. –Sam Sodomsky

“Crescent City”

1988

A popular legend about Lucinda Williams involves her being kicked out of school in 10th grade for refusing to recite the Pledge of Allegiance. A precocious act of protest, it also reflects the seriousness with which she’s always taken her forms of expression. Williams, a lifelong perfectionist, makes music that sways and swells to her own worn-in, deeply human visions of the country. She sings in a low, bluesy drawl that can sometimes sound just half-awake, like the stranger at the bar you have to lean in close to hear. But once you’re keyed to her rhythm, you find yourself hanging on every word.

At the end of the ’80s, Lucinda Williams’ self-titled third album was not an easy sell. Too country for the rock crowd and too heavy for the country folks, her eventual breakthrough record, which she spent eight years composing, seemed like a doomed project. But what some early audiences heard as a flaw, Williams knew was a strength. When it was finally released via Rough Trade, the album’s centerpiece—the swinging singalong “Crescent City,” about her hometown of New Orleans—felt even more triumphant. “This town has said what it had to say,” she sang. “Now I’m headed for that back highway.” Her words rang true; her work ahead would continue to skirt the beaten path with the intensity of someone on a long, mysterious mission, the kind that spans a lifetime. –Sam Sodomsky

“Kerosene”

2005

Forget that Miranda Lambert got her start on a reality TV show—and definitely forget that it was a corny “American Idol” knockoff she didn’t even win. When she made her major-label debut, 2005’s Kerosene, she made sure you knew she was allying herself with the outlaws, with a combustible country-rock sound and a branding-iron voice that could convey defiance, humor, and heartbreak all with equal clarity.

Kerosene’s title track train-robs a melody from Steve Earle’s “I Feel Alright” and doesn’t look back. (Though, fairly, Earle is credited as a cowriter.) It’s a song for the dumped that keeps getting distracted by her skepticism of an industry she seemed reluctant to enter: “Dirty hands ain’t good for shakin’/Ain’t a rule that ain’t worth breakin’.” More than a decade later, Lambert still thrives in a business that only plays 10.4% female artists on the radio, and her defiant attitude has inspired subsequent waves of mainstream and fringe country acts, including her fellow Pistol Annies Ashley Monroe and Angaleena Presley, who are just itching to “light ’em up and watch them burn.” –Stephen Deusner

“In Color”

2008

Before Chris Stapleton brought a bearded tinge of baritone soul to the country charts, there was Jamey Johnson, an Alabama-born, surly-bearded renegade who scored a hit with “In Color” from his second album, That Lonesome Song. Deeply melodic but packed with vibrant, heartbreaking storytelling about the power of memory and the importance of passing tales along from one generation to the other, “In Color” was a classic country outlier in the era of pre-pop Taylor Swift and “Chicken Fried” Zac Brown. (It was a typically unpredictable step from Johnson, who also had a hand in “Honky Tonk Badonkadonk,” Trace Adkins’ ridiculous, borderline offensive bro-country precursor.) The fact that “In Color” fared well, and even scored a Grammy nomination, seems to have convinced Johnson that success is both a blessing and a curse: it’s been eight years since his last album of originals. And, sure, that silence has cost him—but, in country music, freedom itself can be priceless. –Marissa R. Moss

“KMAG YOYO”

2011

Country music has a storied tradition of supporting the military; to some, there’s nothing more American than unflinching pride, even when it shields reality. But Houston’s Hayes Carll wasn’t interested in gesturing when he wrote “KMAG YOYO,” a nod to the acronym used by soldiers to mean “Kiss My Ass Guys, You’re On Your Own.” In the style of Bob Dylan’s “Subterranean Homesick Blues,” Carll wrote about what really happens overseas, and the misguided sort of jingoism and heroism that plagues the interests of so many wars, while also illustrating just how easy is it to lose sense of reality in an environment unimaginable to most of us. Fresh from contributing to the soundtrack of Gwyneth Paltrow’s film Country Strong, “KMAG YOYO” certainly wasn’t Carll’s best chance to keep those new fans he made at the box office—instead, many likely KMAG-ed him right back. And his anthem definitely wasn’t from the cash-cow, flag-waving Toby Keith school, either. But it sure told the truth. –Marissa R. Moss

“Cover Me Up”

2013

Whether he’s country, Americana, or something in between, Jason Isbell is a prime example of how to pave a career with nothing but a set of stellar songs, an ace band, and the determination to do it all on your own. And if that’s not outlaw, what is? After leaving the Drive-By Truckers, Isbell released a string of solo LPs before launching his own Southeastern Records, finding kinship in producer Dave Cobb and getting sober to make his transitional masterpiece Southeastern. With backing from members of the 400 Unit, its opening track, “Cover Me Up,” is a love song so steeped in passion and commitment that it transcends genre altogether, anchored in a simple acoustic strum and Isbell’s voice floating from howl to a quiver. Still a live staple for Isbell, it’s also a benchmark of transformation—for how one album can shape the future of a career, and for how giving something up can mean getting so much in return. –Marissa R. Moss

“You Can Have the Crown”

2013

Sturgill Simpson told theNew York Times a few years ago that, despite the frequent comparisons, he’d never listened much to Waylon Jennings. Either Simpson was pulling our legs or his Waylon doppelgänger vocal on “You Can Have the Crown,” from his pre-fame debut, is among the most miraculous coincidences in pop history. Simpson’s tone and attack, his references to recreational drug use and the musician’s life, even his just-some-good-ol’-boys allusion to watching reruns of “The Dukes of Hazzard”: This is Waylon 101.

At the same time, Simpson’s class consciousness takes him where Jennings rarely ventured. He’s glad he’s struggling to fill the tank of an SUV rather than driving a tank in the Persian Gulf, and he knows his computer searches into the meaning of life will result in just another list of shit he can’t afford. Most current of all are the rhythms driving him, nodding more to punk-aware alt-country than rock-and-swing-loving outlaw country; they’re manic, twitchy, and close to the edge as Sturgill imagines he might actually hold up a bank. Sure, audiences like him, he admits. But at home, his broke ass is still just known as “King Turd.” –David Cantwell

“The Outsiders”

2014

Eric Church and his band’s boasts aren’t really the outsider kind here. As declarations go, calling yourselves “junkyard dogs” and “alley cats” seems quaint; as rebellions go, “we’re the ones burning rubber off our tires” is pretty high-school. As a record, though, “The Outsiders” is pure outlaw, its prime target the bros of mainstream country radio. Where Florida Georgia Line, Luke Bryan, and co. are smooth and self-centered, focused on getting laid and getting buzzed, Church is noisy and self-referential, with thunderous arena beats, screaming guitars, and a bellowed backing chorus; his talk-raps make plain the connections between Charlie Daniels or Hank Williams Jr., say, and hick-hop, the popular country-rap hybrid that’s yet to make a dent at radio. The last section of the record further separates this superstar from the Nashville pack as, following a brief funk-rock segue, his band throws down a pretty fair Metallica imitation. With “The Outsiders,” Church proves himself the rare star trying to change the game from the inside. –David Cantwell

“Hands of Time”

2016

When Margo Price wrote her debut album, Midwest Farmer’s Daughter, she could barely get the time of day from Music Row record labels: It was too traditionally country for modern Nashville, a genre already reluctant to support work from women—especially ones unwilling to shift toward a Hot 100 pop sound. But Price, born in rural Illinois, stuck to her vision, never wavering on her songs like the album opener “Hands of Time,” a six-minute opus that charts her many personal tragedies, including the death of a child and many broken dreams. It returned country music to an era where true storytelling reigned, and it also updated the genre through Price’s smart sense of rock and soul and her urgent, unvarnished production. Since then, Price has made a career out of speaking her mind and staying true to her gut, so it’s no wonder she’s found a kindred spirit in the original outlaw Willie Nelson, who appeared on her second record in the duet “Learning to Lose.” He even let her formulate her own Willie’s Reserve strain of weed. –Marissa R. Moss

“Feathered Indians”

2017

The 27-year-old Tyler Childers’ rise—from years spent chugging on the local Kentucky circuit to opening for John Prine—is one of the most outlaw things about him. Armed with nothing but a set of songs that paint an unshakable picture of both life in modern Appalachia and an uncanny grasp on the meaning of love, he released his Sturgill Simpson and Dave Ferguson-produced debut LP, Purgatory, without any label support and very little traditional media. Since then, he’s amassed a sturdy following, sold-out tours, and streaming numbers that have perplexed an industry that can’t comprehend success unless it comes from a straight-down-the-middle approach. Childers, who grew up on both classic country and grunge, leads by his instincts alone. And it’s his voice, peppered with both the knowledge of the ages and the innocence of youth, that makes a song like “Feathered Indians”—about sex, connection, and the people who finally turn your apathy into optimism —so effective. Then it’s the lyrics, a mix of plain-talk honesty and beguiling metaphors, that tip the scales to timeless. –Marissa R. Moss